537349
Ethyl acetoacetate
ReagentPlus®, 99%
Synonym(s):
EAA, Ethyl 3-oxobutanoate, Acetoacetic ester
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About This Item
Linear Formula:
CH3COCH2COOC2H5
CAS Number:
Molecular Weight:
130.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
205-516-1
Beilstein/REAXYS Number:
385838
MDL number:
eCl@ss:
39022303
Assay:
99%
vapor density
4.48 (vs air)
Quality Level
vapor pressure
1 mmHg ( 28.5 °C)
product line
ReagentPlus®
assay
99%
autoignition temp.
580 °F
expl. lim.
9.5 %
bp
181 °C (lit.)
mp
−43 °C (lit.)
solubility
water: soluble 130 g/L at 20 °C
density
1.029 g/mL at 20 °C (lit.)
functional group
ester, ketone
SMILES string
CCOC(=O)CC(C)=O
InChI
1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
InChI key
XYIBRDXRRQCHLP-UHFFFAOYSA-N
Application
Ethyl acetoacetate is a versatile reagent that can be used as a nucleophile in alkylation, conjugate addition and condensation reactions. Some of its applications are:
- Alkylation at the α-carbon of ethyl acetoacetate followed by hydrolysis and decarboxylation can afford a variety of methyl ketones.
- It also undergoes acylation at the α-carbon in the presence of MgCl2 and pyridine to give synthetically important intermediates.
- It can be used in Knoevenagel condensation with aliphatic, aromatic, and heteroaromatic aldehydes to produce α-alkylideneacetoacetates.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
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Storage Class
10 - Combustible liquids
wgk
WGK 1
flash_point_f
164.3 °F - closed cup
flash_point_c
73.5 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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Knoevenagel-kondensationen mit titantetrachlorid/base?II: Alkyliden-und arylidenacet-bzw.-nitroessigester bei 0?22?.
Lehnert W
Tetrahedron, 28(3), 663-666 (1972)
Ethyl Acetoacetate.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Synthetic Applications of Dealkoxycarbonylations of Malonate Esters, β-Keto Esters, α-Cyano Esters and Related Compounds in Dipolar Aprotic Media-Part II.
Krapcho A P
Synthesis, 1982(11), 893-914 (1982)